Search Results: Vacant Land & Lots in Winter Park for Sale

313 SYLVAN DRIVE
WINTER PARK FL 32789

Land

Days on Market: 137

County: Orange
Legal Subdivision Name: SYLVAN PARK
Waterfront: Yes

Desirable Winter Park, Lake Sylvan lakefront homesite, Sunset views, Lot dimensions 72 x 220 high and dry, .37+ acres custom home building site, quiet brick road, surrounded by other custom homes. FAR 6,494SF + Porches 900SF = 7,394 SF Total available to build before basement SF. Close to Park Ave, Shopping, Schools and Hospitals. New custom home plans are in progress with Floridian Custom Homes.

2379 FORREST ROAD
WINTER PARK FL 32789

Land

Days on Market: 126

County: Orange

This is the last lot in the beautiful Ripples neighborhood, next to Beeman Park and Lake Sue. Build your dream home on this oversized lot with brick streets in the historic district of Winter Park. Zoned for Audubon School District. LOCATION, LOCATION, LOCATION. You are minutes away from the Advent Health complex, Orlando Museum of Art, Orlando Science Center, Mennello Museum, Orlando Repertory Theater, Leu Gardens, Loch Haven Park, Mead gardens, Beeman Park on Lake Sue, the shopping and dining districts of the Ivanhoe Village, the Mills District, College Park, Winter Park, Baldwin Park and Downtown Orlando. This is one ... Read more....»

1756 HOLLYWOOD AVENUE
WINTER PARK FL 32789

Land

New Listing!!!  Days on Market: 1

County: Orange
Legal Subdivision Name: LAKE MONTE SUB

An oversized parcel of land ( 2 1/2 lots ) awaits on a picturesque, tree-canopied street near the Windsong neighborhood. Build a large new Custom home, or given the substantial size of the lot, it might be feasible to pursue an approval to divide it into two separate parcels. If approved, this would provide a buyer with the potential to construct two individual homes - an outstanding prospect for investment.

1000 HOWELL BRANCH ROAD
WINTER PARK FL 32789

Land

Days on Market: 132

County: Orange
Legal Subdivision Name: MAITLAND SHORES SECOND ADD
Waterfront: Yes

Welcome home to 1000 Howell Branch Road, a canal front private oasis. This recently cleared lot is located on an oversized half acre+ lot with a recently dredged fresh water canal frontage, with easy access to Lake Maitland/Winter Park Chain of lakes. Hurry, it’s currently the only vacant lot available on the Chain of lakes. The private backyard is backed up to more than 2 acres of conservation areas, which makes it have an incredible feel. You can be minutes from the hustle and bustle, but step onto the lot and you will feel like you have escaped into your ... Read more....»

7839 UNIVERSITY GARDEN DRIVE
WINTER PARK FL 32792

Land

Days on Market: 4

County: Orange
Legal Subdivision Name: ACREAGE & UNREC
Lot Size (in acres): 4.93

Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417, Winter Park High School, Full Sail University, Barry University, Valencia College, UCF, AdventHealth Hospital, Downtown Orlando, and MCO/Orlando International Airport.

3006 NORTHWOOD BOULEVARD
WINTER PARK FL 32789

Land

County: Orange
Legal Subdivision Name: NORTHWOOD TERRACE

Prime Development Opportunity in Winter Park near Audubon Park. Lot Size - 79' x 103' - 8212 sq. ft. Zoning - R-1A. FAR - 3530. Seize this exceptional opportunity to develop in the heart of one of Winter Park’s most coveted neighborhoods. This 8,212 sq ft lot is ideal for a new construction project or a comprehensive renovation. Surrounded by new and renovated homes, this area is experiencing rapid appreciation. Zoned for Audubon Park K-8 and Winter Park High School, both highly regarded institutions. Enjoy walking distance to local favorites like East End Market, ... Read more....»

2711 PARKLAND DRIVE
WINTER PARK FL 32789

Land

County: Orange
Legal Subdivision Name: PARKLANDO

Rare opportunity to secure a valuable 50'x150' lot in one of Winter Park's most coveted neighborhoods. This property is perfectly positioned for builders and investors looking to capitalize on an unbeatable location. The strategic location offers walking distance to highly-rated Audubon Park K-8 school and steps from the thriving Audubon Park Garden District with established restaurants and boutique shopping. You're minutes from Baldwin Park Village Center with Michelin Star dining, Mills/50 District, and iconic Park Avenue. Situated in a well-established neighborhood experiencing active custom home construction, this represents the perfect opportunity to build new while benefiting from proven market demand.

763 OVERSPIN DRIVE
WINTER PARK FL 32789

Land

Days on Market: 190

County: Orange
Legal Subdivision Name: DUBSDREAD HEIGHTS

Rare lot in Winter Park/College Park just steps away from Dubsdread Golf Course. This location is in Central Florida close to downtown, Winter Park, College Park, Altamonte, all major attractions and the beaches. Centrally located and easy access to I4, and all major roads through Central Florida. The lot frontage is 100'. The lot depth is 140'. You can build the house of your dreams or you can split the lot into two lots by the small lot policy to rezone to R1 according to Orange ... Read more....»

1821 GOODRICH AVENUE
WINTER PARK FL 32789

Land

Days on Market: 65

County: Orange
Legal Subdivision Name: SYLVAN HEIGHTS

Wonderful LOT opportunity to build in prime, quiet location near Windsong and Winter Park Hospital in "active pocket neighborhood" of Winter Park. This 77-by-120-foot lot offers plenty of space to design and build your home or purchase as investment property. Based on the City of WP building worksheet, it appears the lot can accomodate New Construction of a Home apprx 3,700sf FAR + 400sf for front porch + 500sf for side/rear porches + 277sf attic/mechanical storage.... (overall height up to 32 ft) Currently: The property includes a two-bedroom, one-bath single-family home with approximately 1,000 square feet of living space that ... Read more....»

1901 LOCH BERRY ROAD
WINTER PARK FL 32792

Land

Days on Market: 1

County: Orange
Legal Subdivision Name: KENILWORTH SHORES

A rare opportunity in the heart of Winter Park—this property sits on an oversized 0.31-acre corner lot in one of the area’s most desirable neighborhoods. This lot has no rear neighbors offering even more privacy. The existing home is owner-occupied, functional, and will be sold AS-IS, though it will require repairs. The true value lies in the land, offering outstanding potential for renovation, investment, or new construction. The street is experiencing a wave of redevelopment, with new homes selling well over the million-dollar range. Ideally located just minutes from Park Avenue, Baldwin Park, AdventHealth’s state-of-the-art hospital, and the Winter Park ... Read more....»

631 SYMONDS AVENUE
WINTER PARK FL 32789

Land

Days on Market: 19

County: Orange
Legal Subdivision Name: CAPENS ADD

Great R-2 lot in the heart of downtown Winter Park - lot next door 621 Symonds also available for purchase and opportunity to combine.

621 SYMONDS AVENUE
WINTER PARK FL 32789

Land

Days on Market: 19

County: Orange
Legal Subdivision Name: CAPENS ADD

Great opportunity for a R-2 lot in heart of downtown Winter Park - opportunity to purchase adjacent lot at 631 Symonds and combine

7429 RESTFUL STREET
WINTER PARK FL 32792

Land

Days on Market: 43

County: Orange
Lot Size (in acres): 1.96

Expansive 1.96± Acre Vacant Land in Winter Park, FL – Two Lots Sold Together! An incredible opportunity awaits with this 1.96± acre vacant land in highly desirable Winter Park, Florida! This listing includes two lots being sold together, offering ample space to build your dream home, private estate, or a potential development project—all with no HOA restrictions. Ideally located just minutes from downtown Winter Park, Metro Orlando, top-rated schools, shopping, dining, and entertainment, this property combines privacy with convenience. Plus, with easy access to major highways, Orlando International Airport is just a 30-minute drive away. Whether you’re a homeowner looking for the perfect ... Read more....»

229 S EDINBURGH DRIVE
WINTER PARK FL 32792

Land

Days on Market: 100

County: Orange
Legal Subdivision Name: ALOMA

New low price! Fantastic City of Winter Park Location! 8400 square foot lot in the City of Winter Park - "maximum floor area ratio and building coverage shall be 45 percent." Zoned O-2 Professional Office. Perfect for Medical Office/s. Adjacent to Advent Health, Crosby Wellness Center, and Ward Park - a 66.4 acre sports complex. Current improvements include - 2 onsite stormwater retention ponds, existing parking lot, sewage connection. Plans available for a 1785 square foot building. 1 adjacent lot on Dundee with structure currently for sale.

WINTER PARK FL 32789

Land

Days on Market: 1

County: Orange
Legal Subdivision Name: ORWIN MANOR WESTMINSTER SEC

Fabulous location in one of Winter Park's most sought-after neighborhoods. Orwin Manor features tree-lined streets and historical homes just minutes from Park Ave, Hannibal Square, Rollins College, premier restaurants and shoppes, and quick access to I-4.

786 W CANTON AVENUE
WINTER PARK FL 32789

Land

Days on Market: 430

County: Orange
Legal Subdivision Name: CAPENS ADD

Back on the Market! Buyer could not perform. This is a Perfect high and dry lot with a tree to shade your backyard. Nestled in the highly sought after City of Winter Park amongst million dollar homes. A perfect home site for your future custom home. Bring your imagination creativity and builder to take a look. What a Winter Park sweet spot. Lots in this area are HARD to come by. Ride your bike to Park Avenue or just walk/stroll over to the Winter Park Village. Your search is over, this is it. There is a NEW HOME community right ... Read more....»

1807 MAGNOLIA AVENUE
WINTER PARK FL 32789

Land

Days on Market: 64

County: Orange

Build your dream home in the City of Winter Park! This deep 56x157 lot is Winter Park’s best kept secret, located in a quiet pocket of 32789, with beautiful trees and no HOA. This property is centrally located, less than 10 minutes to Park Ave, and zoned for Orange County schools: Dommerich Elementary, Maitland Middle and Winter Park High School. A custom home just went up around the corner in this neighborhood (built in 2023) – yours could be next! Act now, it is rare to find land at this price in this zip code. The purchase of ... Read more....»

3520 WILDE AVENUE
WINTER PARK FL 32792

Land

Days on Market: 12

County: Orange
Lot Size (in acres): 1.01

Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just over an acre, lot in coveted Winter Park. Nestled on the end of a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a private maintained road with NO HOA and NO CDD. Zoned A-2 with the opportunity to add an additional workshop, barn, or ADU. Bring your chickens and ... Read more....»

3580 WILDE AVENUE
WINTER PARK FL 32792

Land

Days on Market: 5

County: Orange

Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a private maintained road with NO HOA and NO CDD. Zoned A-2 with the opportunity to add an additional workshop, barn, or ADU. Bring your chickens and grow your garden ... Read more....»

987 CHEROKEE AVENUE
WINTER PARK FL 32789

Land

County: Orange

The landlord seeks a long term tenant or a joint venture from a developer or someone with a home to move. Contact us now and let's discuss this opportunity. Incredible opportunity to bring your own home to this prime Winter Park building lot with all utilities stubbed at the curb from a previous home that was removed. The current owner of 987 Cherokee Avenue, Winter Park is willing to lease the lot zoned R-3 and give a long term tenant a purchase option or a first right of refusal. This lot allows for relocation of a single family home, or a modular ... Read more....»